Tertiary alkyl phenols



Patented May 25, 1937 TERTIARY ALKYL PHENOLS Frits E. Stockelbach, Montclalr, N. .L, asslgnor to Harold H. Fries, doing business as Fries Bros, New York, N. Y.

Serial No. 616,493

No Drawing. Application June 10, 1932,

Claims. (01. coo -154) The present invention relates to compounds suitable for use as antiseptics, disinfectants, germicides and the like and more especially it relates to such substances that areobtainable by the 5 reaction of a phenolic compound with a tertiary alcohol, and constitutes a continuatiomin part, of my application, Serial No. 572,219, filed October 30, 1931.

In my aforementioned application I have disclosed that the introduction of a tertiary alkyl radical into meta cresol increases the germicidal value of said phenol many fold.

I have now carried by investigations further and have determined the effect of the introduction of the tertitary alcohol 'radical mm the nucleus oi! the various phenols present in coal tar and find that in all instances examined that the germicidal value of the teritary alkyl substituted phenols is materially greater than the germicidal value oi the corresponding phenols prior to the introduction thereinto of the tertiary alkyl radical. The phenolic compounds which I have investigated are the following:

Degrees centigrade Plm'mnl melting point 39 UresolU. S. P boiling range 196-202 'Cresylic acid-crude bolling range 201-216 Cresylic acid-crude' boi1ing range 203-225 xylenol --boiling range" 212-222 All of the foregoing phenolic compounds are commercially available products from the refining I of coal and gas tar. v

The method of preparing the tertiary alcohol substitution products is best carried out through the condensation of the corresponding tertiary alcohol with the phenolic compound, using a suitable condensing agent, such, for example, zinc chloride. In carrying out the condensation reaction, the phenolic compound, the tertiary alcohol and zinc chloride are heated with constant stirring until the reaction is complete, which 5 requires two or three hours. The reaction products consist of mixtures of mono and di-substituted tertiary alkyl phenols, and they are purifled after careful washing by fractional distillation in vacuum. 1

Examples of the products obtained from the live phenols aforementioned wherein tertiary butyl alcohol is employed as the tertiary alkyl producing radical, are given below with their 55 physical constants:

Tertiary butyl phenol Crystalline compound; congealing point 76 C. v

Tertiary butylatecl cresol U. s. P. T

Spec. gravity ..9662 at 20 0.

Optical rotation -E +.2 at 25 C.

Refractive index 20 C 1. 5207 Boiling range 760 mm.. 240-253 C.

Tertiary buty'lated cresylic acid crude m Spec. gravity at 20 .9673

Optical rotation 25 +.1

Refractive index 20 C 1.5217

Boiling range 760 mm 237-257 C. 15

Tertiary butylated cresylic acid crude Spec. gravity at 20 .9691

Optical rotation: 25 +.1

Refractive index 20 1.5220 20 Boiling range 760 mm 238-259 C.

Butylated splenol Specific gravity 20 .9613

Optical rotation +.1 25

Refractive index 20 1.5205

Boiling range 760 mm 250-265" C.

The phenol substitute is a para compound. As cresol U. S. P. and crude cresylic acid consist of mixtures of ortho, meta and para cresols and as the xylenol also contains various isomers, the

position of the tertiaryalkyl radical in these alkyl substituted phenols is not determinable.

Bacteriological tests of the original phenols and of the tertiary butyl substitutes are shown in the following table, the phenol coeflicients having been determined according to the Food and Drug Administration Method as published in the United States Department of Agriculture Circular No. 198 using staphylococcus as testing organism:

Phenol. coemcient Tertiary butylated xylenol 150.0

Tertiary amyl alcohol may be used in a way similar to tertiary butyl alcohol in obtaining antiseptics and germicides of the class described. The condensation products obtained with tertiary g amyl alcohol, however, do not have as high a phenol coefficient as the corresponding phenol condensation products with tertiary butyl alcohol.

From the foregoing detailed description it will 10 be appreciated that I have discovered a new class of powerful antiseptics and germicides, and it is not intended that any one particular compound produced in any of these condensation reactions shall be isolated for use but that a certain 15 fraction or fractions boiling over a fairly wide temperature range shall be taken for such use. In cases, however, where the condensation product consists mainly of one compound which may be easily brought to a high degree of purity by 20 fractional distillation, such particular compound may be isolated. Hence the invention is not to be considered as limited to the specific compounds and condensation products enumerated, but is applicable to antiseptics and germicides 25 comprising as a constituent thereof the condensation products of a phenolic compound and a tertiary alcohol, and more particularly to the condensation products of commercial phenols, for example, those derived from coal tar and tertiary butyl alcohol.

What I claim is:

1. The nuclear alkylated condensation products of a mixture of commercial phenols derived from coal tar and a tertiary alcohol.

2. The nuclear alkylated condensation products of a mixture of commercial phenols derived from coal tar and tertiary butyl alcohol.

3. The condensation product of cresol U. S. P. having a boiling range from 196--202 C. with tertiary butyl alcohol, the said condensation product having a boiling range of 240253 C.

4. The condensation product of crude cresylic acid having a boiling range from 20l-216 C. with tertiary butyl alcohol, the said condensation product having a boiling range of 237-257 C.

5. The condensation product of xylenol having a boiling range from 212-230 C. with tertiary butyl alcohol, the said condensation product having a boiling range of 250-265 C.

FRITS E. STOCKELBACH. 

